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Leading Your Family During Retirement

Many squander the chance to lead their families during retirement and lose massive opportunities for fulfillment and happiness. As you embrace your ability to lead your children and grandchildren during retirement, your family can have greater unity and your retirement years can take on much more significance.

Relationships with children and grandchildren can be some of the most powerful and important relationships we experience but can also cause some of the deepest wounds. No matter where your relationships currently reside with your loved ones, your retirement years give you a new chapter to level up those relationships that matter most.

Leadership in the workplace is often discussed and praised yet society rarely emphasizes leadership in the home. Often media and pop culture downplay the role of strong parents and grandparents, emphasizing dysfunction instead. 

The truth is that grandparents who retire enter a unique phase of life to influence and lead their families in unprecedented ways. Instead of letting your most important relationships evolve through chance, seize the possibility to unite your family, create incredible memories, and leave an intentional legacy embedded with the values that will help your family thrive for years to come

As you mold and shape retirement, here are five powerful strategies to help you lead your family during retirement:


“The greatest danger for most of us is not that our aim is too high, and we miss it, but that it is too low, and we reach it.”

"Leadership is the capacity to translate vision into reality.”

Most businesses develop vision statements and know the significance of leading with vision. Where do we want to go? What are we trying to achieve? When do we want to get there? The professional business world is ripe with vision statements and goal setting. Somehow, this rarely translates into leadership in the home, especially during retirement.

I once heard a story of a single father, who was less than happy about his seventeen year old daughter’s choice in a boyfriend and was letting her know it. Instead of coming closer together, their relationship was being strained and he knew it. So what was he to do?

He decided to tackle the issue by finding something new and exciting that he knew his daughter was interested in. She had expressed interest in volunteering in third-world countries so the two of them scheduled a trip. 

This trip inspired her to see a bigger vision for her life and what she wanted to do after high school. She realized pretty quickly that her boyfriend didn’t match her vision for a greater future and they drifted apart.

One way to do this is to clearly articulate your family values and principles. One suggestion is to have a family dinner or barbecue. Get everyone together and take a few minutes to lead a discussion on what your family stands for. Look for consensus and something everyone can buy into. You could even pass out a sheet with twenty different values or statements and have family members circle what’s most important to them (i.e. hard work, integrity, growth, courage, faith, etc).  Identify at least five values and formalize them in some way. One way to make this more concrete way is to create a Family Vision Statement.

Whether your family vision is an informal discussion or formalized in an actual document, helping your family see a bigger vision can create unity and excitement.


“A nation’s culture resides in the hearts and in the soul of its people.”

Your family culture is what you do, how you do it, and how you treat each other. For example, what do you do during the holidays and Christmas season? What will you do for Thanksgiving? How often will you reach out to your children and grandchildren? What influence will you have on their life? How does your family handle conflict? What will you do for birthdays?

Four of our six children have now finished high school and are creating their own lives. As three of them have now left home my wife and I found that we weren’t connected nearly as often as we would like. We created a monthly family fireside where we regularly eat together and have meaningful discussion. 

At an even higher level, we met about a year ago as a family and asked specific questions about what our family culture would be like ten years in the future. We wanted to get everyone’s input. Our daughter-in-law was also included.

Here are the five questions we asked:

  • What is our family’s greatest strength?
  • What positive feelings or emotions do we want people to feel around our family?
  • What trips, events, and experiences do we want to have as a family?
  • We… (complete the sentence)
  • I will make this family better by… (complete the sentence)

This created an amazing opportunity to have everyone contribute and buy into the Woolston family future. We discussed how often we would get together once they all left home, what kind of grandparents we want to be (2nd grandchild is on the way), and amazing experiences we wanted to have together. There was a ton of excitement and buzz as we had an amazing brainstorming session. Best of all, it wasn’t just my vision or Christy’s (my wife). Our plan is to make this an ongoing discussion.


“A leader is one who knows the way, goes the way, and shows the way.”

A family vision and culture isn’t just inspirational or motivational, it’s something you are and are dedicated to becoming. Leading from the front means that you lead by example and are willing to do the tough things first, not waiting for everyone else to do them.

For example, if one of your core values in your family is learning and growth but you refuse to read a book, share something you’re learning, or are unwilling to change, you’re expecting everyone else to do the work.

Great leaders work in the trenches not in the clouds.

My parents, who are over seventy now, have an amazing work ethic and service mindset. No matter what is needed, they are always willing to help paint a room, fix some plumbing, or make some food if someone is sick. They always have a project and are making upgrades to their house and yard. When we were young, my siblings and I were always working in the garden, in the yard, or around the house. But none of us worked harder than my parents. They led from the front and my older sister and three younger brothers have all developed an amazing work ethic. They make a powerful couple and lead by action.

Our examples are much more powerful than what we say. It’s who we are. When we lead with vision and then back it up with our efforts, we can inspire and motivate those around us.


“Enjoy life. There’s plenty of time to be dead.”

Getting the attention of young people can be one of the most difficult challenges we face, especially in the age of instant gratification and technology. When I was young, if someone mentioned hiking or going and doing something fun, I was all over it. I didn’t have the list of competing options that exist today such as movies, video games, cell phones, or social media.

Today we’re competing for attention at a whole new level.

I’d suggest planning amazing and fun experiences that are designed all around creating memories. 

Here are some ideas:

  • Take your grandkids to lunch for their birthday instead of a present
  • Invite your grandchildren over for a party or to stay the weekend
  • Take a vacation together
  • Invite your grown children to lunch one-on-one 
  • If your children and grandchildren don’t live near you, have a regular Zoom call
  • Go to the lake or mountains and go boating or exploring
  • Do a weekend getaway with a specific grandchild and plan the weekend together
  • Go see a concert or play together
  • Plan a family reunion
  • Take a road trip
  • Have a campfire and tell scary stories

When working with clients and making goals about estate and legacy planning, often the discussion can center around the money. While this is important and necessary, creating memories with those you love can be much more valuable and lasting.


“The best thing to hold onto in life is each other.”

Early in my career, when my wife and I were just starting our family, I had the opportunity to ask over fifty individuals who had raised children (many of them were grandparents), what the secret to raising children was. Over and over again, the response was simply to love them, no matter their choices.

Candidly, at times I’ve tried to fix the people around me instead of loving them first. When I catch myself doing that I try to remind myself that fixing people (even with the best of intentions) comes from the lens of problem solving. People aren’t a problem to solve but rather a person to love. When I lead with the lens of love, lifting or elevating them becomes a natural bi-product. I have a long way to go with this principle and am a work in progress but have found this concept to be powerful. 

How can you love your children and grandchildren where they are at? How can you show them? Do they know you’ll love them, no matter their choices? Have you told them? This principle will amplify any efforts you make toward leading your family during retirement.


As you retire you’ll enter a unique phase of life to influence and lead your children and grandchildren in unprecedented ways. Are you going to mold and shape the culture of your family or let it happen by chance? What does your family stand for? As you intentionally lead from the front you’ll get greater buy-in. Lastly, work toward creating memories and letting those close to you know how much you love them.

Do you have a plan to transition into retirement? Do you understand it? Are you confident in your plan? Learn more about how we help our clients replace their paycheck income, manage their investments, and minimize retirement taxes. Do you have questions about when to take Social Security and how to maximize your benefit? Take our free online Social Security Masterclass.